When comparing Cloak vs LastPass, the Slant community recommends Cloak for most people. In the question“What are the best power user tools for macOS?”Cloak is ranked 30th while LastPass is ranked 37th. The most important reason people chose Cloak is:

SSL pinning protects against some forms of man-in-the-middle attacks that even SSL encrypted traffic is vulnerable to. Not long ago, iOS did not allow for pinning but that may have changed more recently.

Pros

Pro

Does SSL Pinning on OS X

SSL pinning protects against some forms of man-in-the-middle attacks that even SSL encrypted traffic is vulnerable to. Not long ago, iOS did not allow for pinning but that may have changed more recently.

Pro

Responsive developer

The developer of Cloak is extremely responsive to feedback and quick to answer questions or support requests.

Pro

Senses Trusted WiFi networks

Cloak can be set to not use the VPN on whitelisted WiFI SSIDs (like home/work).

Pro

Unlimited devices (as long as they're OSX/iOS)

Unlimited devices and data per account, so you can connect up the whole family or office on one account if you so choose.

Pro

Automatic cloud backup and cross-device sync

LastPass keeps an encrypted copy of all passwords locally as well as an encrypted copy on their servers. That way, passwords can be accessed locally while offline, or through their server while online from any machine.

Pro

Seamless autofill and password generator via plugins for all popular browsers

All common browsers, including Opera, have plugins that allow automatically filling in forms and generating passwords. All form fill information syncs across all platforms, devices and browsers. Password generator can be adjusted to use or exclude certain characters and patterns.

Pro

All encryption and decryption is done locally

All the encryption and decryption is done by the client (JS/App) so even LastPass doesn't have access to passwords.

Pro

Works with portable versions of Chrome and Firefox

Firefox 2+ on Windows, Mac & Linux as well as Chrome 4+ on Windows and Linux support a portable version of LastPass. Great for securely accessing LastPass Vault from public or untrusted computers.

Pro

Works on Linux

LastPass alongside KeePassX are the only cloud-syncing password managers that work on Linux.

Pro

Clean and intuitive UI

Since version 3.0 the LastPass interface is clean and easy to navigate on all platforms.

Pro

Automatic security monitoring

LastPass will check for re-used and unsafe passwords.

Pro

Does not require a standalone app

While many password managers require a standalone app to be installed on the system, LastPass does not and can function via browser plugins.

Pro

Fingerprint verification

Some fingerprint readers, like TouchID on iOS devices or on Samsung devices, can be set up to be used to access LastPass instead of a master password.

Pro

Allows sharing passwords with one person or a group of people

LastPass allows sharing login data for a site with another user of LastPass without exposing the password. Great for allowing friends, family or coworkers access a site.

Pro

Yubikey Support

Pro

Password One-Click Change

LastPass is able to change your password automagically.

Pro

Offers multiple export options

LastPass can dump the whole database as a .csv file or an encrypted file that can then be decrypted using LastPass Pocket as well as separately export Wi-Fi passwords and autofill information. Additional export options are available on a per-browser basis.

Pro

Can create one-time passwords for accessing the Vault

LastPass allows creating passwords for accessing the LastPass Vault that can only be used once. Great for accessing the Vault in public or untrusted places.

Pro

Vetted by Steve Gibson

Steve Gibson is a well established security researcher best know for his work with Apple and Atari systems as well as founding Gibson Research Corporation. He was given access to LastPass' source code and confirmed that it's safe to trust its security.

Pro

Allows downloading an encrypted database backup that can only be decrypted with LastPass Pocket

LastPass Pocket is a standalone personal database decrypter. It's a portable executable, meaning it does not need to be installed, that is used to decrypt a local encrypted copy of the password database.